Raddeanin ACAS# 89412-79-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 89412-79-3 | SDF | Download SDF |
| PubChem ID | 343425 | Appearance | White powder |
| Formula | C47H76O16 | M.Wt | 897.11 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | DMSO : 50 mg/mL (55.74 mM; Need ultrasonic) | ||
| Chemical Name | 10-[3-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid | ||
| SMILES | CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(COC3OC4CCC5(C(C4(C)C)CCC6(C5CC=C7C6(CCC8(C7CC(CC8)(C)C)C(=O)O)C)C)C)O)O)CO)O)O)O)O)O | ||
| Standard InChIKey | VQQGPFFHGWNIGX-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C47H76O16/c1-22-30(50)33(53)35(55)38(59-22)62-37-34(54)32(52)26(20-48)60-40(37)63-36-31(51)25(49)21-58-39(36)61-29-12-13-44(6)27(43(29,4)5)11-14-46(8)28(44)10-9-23-24-19-42(2,3)15-17-47(24,41(56)57)18-16-45(23,46)7/h9,22,24-40,48-55H,10-21H2,1-8H3,(H,56,57) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Raddeanin A, a histone deacetylases (HDACs) inhibitor, has high antiangiogenic potency, and antitumor activity, it can suppress the growth of liver and cells, it also inhibits proliferation of GC cells (BGC-823, SGC-7901 and MKN-28), induces their and inhibits the abilities of invasion, migration. |
| Targets | VEGFR | JAK | FAK | Src | Akt | HDAC | Bcl-2/Bax | Caspase | PARP | MMP(e.g.TIMP) |
| In vitro | Raddeanin A, a triterpenoid saponin isolated from Anemone raddeana, suppresses the angiogenesis and growth of human colorectal tumor by inhibiting VEGFR2 signaling.[Pubmed: 25636878]Phytomedicine. 2015 Jan 15;22(1):103-10.Raddeanin A (RA) is an active triterpenoid saponin from a traditional Chinese medicinal herb, Anemone raddeana Regel. It was previously reported that RA possessed attractive antitumor activity through inhibiting proliferation and inducing apoptosis of multiple cancer cells.
However, whether RA can inhibit angiogenesis, an essential step in cancer development, remains unknown.
Raddeanin A induces human gastric cancer cells apoptosis and inhibits their invasion in vitro.[Pubmed: 23988447]Biochem Biophys Res Commun. 2013 Sep 20;439(2):196-202.Raddeanin A is one of the triterpenoid saponins in herbal medicine Anemone raddeana Regel which was reported to suppress the growth of liver and lung cancer cells. However, little was known about its effect on gastric cancer (GC) cells.
This study aimed to investigate its inhibitory effect on three kinds of different differentiation stage GC cells (BGC-823, SGC-7901 and MKN-28) in vitro and the possible mechanisms.
|
| Kinase Assay | Synthesis and biological evaluation of Raddeanin A, a triterpene saponin isolated from Anemone raddeana.[Pubmed: 25087630]Chem Pharm Bull (Tokyo). 2014;62(8):779-85.First, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors.
|
| Structure Identification | J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 1;923-924:43-7.Determination of Raddeanin A in rat plasma by liquid chromatography-tandem mass spectrometry: application to a pharmacokinetic study.[Pubmed: 23455073]A simple, rapid and sensitive LC-MS/MS analysis method was developed and validated for the determination of Raddeanin A (RA) in rat plasma. Protein precipitation with three volumes of methanol as the precipitation reagent was used as the sample preparation method.
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Raddeanin A Dilution Calculator
Raddeanin A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.1147 mL | 5.5735 mL | 11.1469 mL | 22.2938 mL | 27.8673 mL |
| 5 mM | 0.2229 mL | 1.1147 mL | 2.2294 mL | 4.4588 mL | 5.5735 mL |
| 10 mM | 0.1115 mL | 0.5573 mL | 1.1147 mL | 2.2294 mL | 2.7867 mL |
| 50 mM | 0.0223 mL | 0.1115 mL | 0.2229 mL | 0.4459 mL | 0.5573 mL |
| 100 mM | 0.0111 mL | 0.0557 mL | 0.1115 mL | 0.2229 mL | 0.2787 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Raddeanin A induces human gastric cancer cells apoptosis and inhibits their invasion in vitro.[Pubmed:23988447]
Biochem Biophys Res Commun. 2013 Sep 20;439(2):196-202.
Raddeanin A is one of the triterpenoid saponins in herbal medicine Anemone raddeana Regel which was reported to suppress the growth of liver and lung cancer cells. However, little was known about its effect on gastric cancer (GC) cells. This study aimed to investigate its inhibitory effect on three kinds of different differentiation stage GC cells (BGC-823, SGC-7901 and MKN-28) in vitro and the possible mechanisms. Proliferation assay and flow cytometry demonstrated Raddeanin A's dose-dependent inhibitory effect and determined its induction of cells apoptosis, respectively. Transwell assay, wounding heal assay and cell matrix adhesion assay showed that Raddeanin A significantly inhibited the abilities of the invasion, migration and adhesion of the BGC-823 cells. Moreover, quantitative real time PCR and Western blot analysis found that Raddeanin A increased Bax expression while reduced Bcl-2, Bcl-xL and Survivin expressions and significantly activated caspase-3, caspase-8, caspase-9 and poly-ADP ribose polymerase (PARP). Besides, Raddeanin A could also up-regulate the expression of reversion inducing cysteine rich protein with Kazal motifs (RECK), E-cadherin (E-cad) and down-regulate the expression of matrix metalloproteinases-2 (MMP-2), MMP-9, MMP-14 and Rhoc. In conclusion, Raddeanin A inhibits proliferation of human GC cells, induces their apoptosis and inhibits the abilities of invasion, migration and adhesion, exhibiting potential to become antitumor drug.
Synthesis and biological evaluation of Raddeanin A, a triterpene saponin isolated from Anemone raddeana.[Pubmed:25087630]
Chem Pharm Bull (Tokyo). 2014;62(8):779-85.
First, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors. The chemical structure of Raddeanin A was confirmed by means of (1)H-NMR, (13)C-NMR, IR, MS and elemental analysis, which elucidated the structure to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabino pyranoside oleanolic acid. Biological activity tests showed that in the range of low concentrations, Raddeanin A displayed moderate inhibitory activity against histone deacetylases (HDACs), indicating that the HDACs' inhibitory activity of Raddeanin A may contribute to its cytotoxicity.
Determination of Raddeanin A in rat plasma by liquid chromatography-tandem mass spectrometry: application to a pharmacokinetic study.[Pubmed:23455073]
J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 1;923-924:43-7.
A simple, rapid and sensitive LC-MS/MS analysis method was developed and validated for the determination of Raddeanin A (RA) in rat plasma. Protein precipitation with three volumes of methanol as the precipitation reagent was used as the sample preparation method. The analysis process was performed on a Thermo Syncronis C18 column with the mobile phase of methanol-water (containing 5mM ammonium formate, pH 2.2) (85:15, v/v). RA and glycyrrhetinic acid (internal standard) were monitored under negative electrospray ionization in multiple reaction monitoring (MRM) mode. Retention time of RA and IS were 2.1 min and 3.5 min, respectively. The limit of detection was 5 ng/mL and the linear range was 50-50,000 ng/mL. The intra-day and inter-day precision was 1.87-2.94% and 3.25-5.36%, and the intra-day and inter-day accuracy ranged from 5.9% to 10.5% and 5.6% to 11.1%, respectively. The absolute recovery was above 90.3%. The method has been successfully translated to the pharmacokinetic study of RA in rats after intravenous and intraperitoneal administration (0.75 mg/kg).
Development and validation of a sensitive liquid chromatography/tandem mass spectrometry method for the determination of raddeanin A in rat plasma and its application to a pharmacokinetic study.[Pubmed:23290921]
J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Jan 1;912:16-23.
A simple and sensitive high-performance liquid chromatography-electro-spray ionization tandem mass spectrometry (LC-ESI-MS/MS) method was developed and validated to determine Raddeanin A in rat plasma. After precipitation of rat plasma samples with methanol, chromatographic separation was achieved on a BDS Hypersil C18 column (100x2.1mm, 2.4mum) using the mobile phase consisted of acetonitrile and 2mM ammonium acetate with 0.05% formic acid (60:40, v/v). The detection was performed in a triple quadrupole tandem mass spectrometer by multiple reaction monitoring (MRM) mode using negative ionization. The transition monitored were m/z 895.6-->455.0 for Raddeanin A and m/z 359.3-->329.0 for IS, respectively. The method was linear over the concentration range of 2-1000ng/mL for Raddeanin A. The intra-day and inter-day assay variations were <9.46%, and the accuracy values were between -2.04% and -6.52% relative error. The extraction recovery of Raddeanin A was more than 70%, and the relative matrix effect ranges from 108.52% to 112.36%. The validated method has been successfully applied to determine the pharmacokinetic profile of Raddeanin A in rat plasma following oral and intravenous administration.
Raddeanin A, a triterpenoid saponin isolated from Anemone raddeana, suppresses the angiogenesis and growth of human colorectal tumor by inhibiting VEGFR2 signaling.[Pubmed:25636878]
Phytomedicine. 2015 Jan 15;22(1):103-10.
Raddeanin A (RA) is an active triterpenoid saponin from a traditional Chinese medicinal herb, Anemone raddeana Regel. It was previously reported that RA possessed attractive antitumor activity through inhibiting proliferation and inducing apoptosis of multiple cancer cells. However, whether RA can inhibit angiogenesis, an essential step in cancer development, remains unknown. In this study, we found that RA could significantly inhibit human umbilical vein endothelial cell (HUVEC) proliferation, motility, migration, and tube formation. RA also dramatically reduced angiogenesis in chick embryo chorioallantoic membrane (CAM), restrained the trunk angiogenesis in zebrafish, and suppressed angiogenesis and growth of human HCT-15 colorectal cancer xenograft in mice. Western blot assay showed that RA suppressed VEGF-induced phosphorylation of VEGFR2 and its downstream protein kinases including PLCgamma1, JAK2, FAK, Src, and Akt. Molecular docking simulation indicated that RA formed hydrogen bonds and hydrophobic interactions within the ATP binding pocket of VEGFR2 kinase domain. Our study firstly provides the evidence that RA has high antiangiogenic potency and explores its molecular basis, demonstrating that RA is a potential agent or lead candidate for antiangiogenic cancer therapy.
